The Letter
by Sarah Jae
Summary: The letter that Rory *ALMOST* sent to Jess in "Those Lazy-Hazy-Crazy Days" and the letter which is how I imagine Jess responds.
1. The Letter

Dear Jess,

I'd better get to the obvious first. Sookie and Jackson's wedding- that was... I honestly couldn't tell you. I don't have a clue what I was thinking, but it just seemed right. I like you, and I hope that you know that now.

Wow, I can't believe I actually just let myself write that. I've been trying to keep it a secret from... Well, everyone, for a long time.

But there's Dean. I still love him- I think.

God, I don't even know anymore. I mean, he's great and all, but you... You're special.

I wasn't mad when you took/returned "Howl" with your notes in the margins. It was a wake-up call. Dean wasn't what I needed. You were.

Again, I can't believe I just wrote that.

Even though I have definite feelings for you, I'd really appreciate it if you wouldn't tell anyone about the kiss. The kiss. It sounds so formal.

I know you already agreed to this, but repetition is a great way to remember.

I'm not sure how you feel about what happened, if you want to go and brag to Dean and make him hate you even more. But you're not a jerk- I think.

All of these "I thinks" and "Maybes". If there was one thing I needed to be sure about, it would be this.

And now I'm not even sure if I'm going to send this. But I'm worried that if I don't, you'll have moved on.

How do I know if you even like me?! I kissed YOU. Not the other way around.

I feel like an idiot. Why should I leave the guy who's loved me for almost 3 years for a friend... Not even a friend. But a guy that I have a little bit of a crush on.

Right- I don't love him anymore.

I didn't write that. I CAN'T believe I just wrote that.

Sorry if I'm being redundant. I just have a lot to say.

Washington's okay, but Paris is driving me crazy. If I EVER have to room with her again, someone is going to be severely injured.

I'll see you soon. I hope. I mean, I know I'll see you, but I don't know under what circumstance. Will you be my friend, my enemy... My boyfriend?

It doesn't matter. I guess I'll just see you.

Sincerely, Yours, Love, Whatever.

Rory


	2. The Response

**Thanks to ****Midnight-Gypsy101****, I wrote a responding letter. Enjoy!**

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Dear Rory,

Do you honestly think that low of me?

Why do you think that I came back to Stars Hollow, of all places? Did you think I missed the school? The _festivals_? No. No WAY.

Rory Gilmore, I missed _you_.

Ever since that night when we got ice cream and Luke sent me away, you've been all I thought about- not that it wasn't that way before. You're the only person in this mental institution of a town that I can have a conversation with without wanting to mock mercilessly. That might be because we share an interest (reading), or it might be because I really like you.

And maybe it's a little of both.

"I CAN'T believe I just wrote that"

That's just a little playful mocking. I hope you picked up on it.

What I'm saying is that I like you too, and I hope that you haven't changed your mind about Dean/me since you wrote the last letter.

Oh, and is Paris the one who was so sure that I worshiped Kerouac and Bukowski and never read Jane Austen (even though I HAVE read Jane Austen) when I was at your house? I can see how it'd be hard to live with her in a dorm for 2 weeks. Or spend more than 2 hours with her at a time.

Just make the right decision, and I'm going to say "please" because I'm dying here.

"Sincerely, Yours, Love, Whatever,"  
Jess


	3. The Letter 2

**Thanks for all the great reviews! Here's what was asked for :)**

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Dear Jess,

You have no idea how happy it makes to hear you say that. I mean, I kind of suspected it, but I wasn't sure. God, that makes me sound so conceited. I thought you liked me.

I should really rewrite these things before I send them, but frankly, I'm too tired, and if I don't send them right as I write them, I'll chicken out.

Why am I so scared of you? You've been my friend for almost a year. I should be able to write you and not be afraid of what you'll think.

I'm going to cut to the chase here and stop talking about my feelings, because I can practically see you smirking.

So anyway, it's really, really interesting here. I'm meeting all these amazing people, ones who were my idols when I was a kid and even now- that is if Paris hasn't scared them away yet. You see, she's kind of intimidating, and the politicians are used to the starry-eyed-politically-aware teenagers who just call them role models and stuff. Paris asks serious questions. You know, the ones Press Secretaries avoid.

There's also this guy that totally likes her, Jamie, and she's oblivious. Actually, he asked her out tonight, and she didn't know it until I told her. They're out now, but she made me hide in the closet after I helped her get ready, because apparently, I'm too much of a threat with my features. I wanted to laugh.

So I guess that's it. I'll see you next week.

Love,

Rory


	4. The Response 2

**Hey, sorry about the late updates. I've been going through a lot lately. Thanks for the great reviews!**

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Dear Rory,

Quite honestly, you have no reason to be scared of me. I'm a normal guy, not Michael Myers. It's not like I'm going to crash your car.

Kidding. Still sorry about that, by the way. Your arm looked fine when I saw you at the wedding, so I guess you're okay. Unless you have some kind of brain damage... But I'd have heard about that. Probably.

Ah, this waiting is killing me. Are you okay?

Of course you're okay. The Stars Hollow Gazette would have had a tribute to "Rory-Minus-Hoodlum" running daily if you weren't.

And it's not like I do anything that bad. I think my worst crime was attempting to make friends with the town sweetheart while disliking her 38-foot-tall boyfriend that Ward and June would approve of.

I really hate that guy, you know? Had nothing against him until he had a problem with me.

It actually amuses me, his jealousy. Every time I'm around you and him it looks like he's going to turn in to The Hulk if I dare speak. Which I do, not only to talk to you but to see his reactions.

I never really meant to get him mad, but now it's just too funny.

And you really just made me crack up. Do you really think Paris has _anything_ on you physically? You're beautiful in every way, and Paris is... Intimidating. And slightly scary.

So I guess I'll go now. I'll see you soon.

Miss you,

Jess


	5. The Letter 3

**As much as I hate to do this, I want to keep it as close to the actually storyline as possible. It actually hurt me to write this, because I'm totally Literati. And for those who are wondering, I have a plan for the end (which is the next chapter). I'm just not going to say it now :)**

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Jess-

What am I thinking?! Dean is my steady, dependable, amazing boyfriend. Why am I acting on a crush?! You're great, and you know that, but I don't know if I can put myself through a breakup right now.

Dean and I could end up _married_. Our relationship has SO much potential, and I have to stop thinking about you as more than a friend because you _aren't_.

You know I love you, right? Not like I love Dean, but like I love a friend- a BEST friend. That's all we're meant to be, ever. And I have to convince myself of that or I won't be able to come back home.

It's more of a brother-sister thing now that I think about it. We bicker, we make up. It's an endless circle, but I like it, and I don't want things to change.

Please don't hate me. I'm really trying to do what's best for everyone. It doesn't matter what I want, and I certainly don't want to leave Dean for the guy that he hates.

Can't you try to get along with him? Please? I need my best friend and my boyfriend to get along or life is just going to suck.

I feel terrible for giving you the wrong idea. I feel terrible for writing these letters. Can you ever forgive me?

I really hope so, because as much as I love Dean, I love you, too. I can't have both of you, so-

AH! There I go again! I don't love you as more than a friend.

I need to keep telling myself that or else I won't believe it.

Please still be in my life, Jess. I want you there.

Love,

Rory


	6. The Response 3

**Final Chapter. Sorry for late update, I couldn't bring myself to write this.  
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Rory-

You're being funny, right? Because I know that you do that, a lot. I mean, come on, Rory Gilmore would never tease a guy for half a summer and then just give him a "just kidding".

This is ridiculous, Rory. Were you lying to me this whole time? Was the whole thing some kind of sleepover-esque dare?

Ha. You LOVE me. I'm your BEST friend. If you love me and I'm your best friend, then why are you so set on making me as miserable as possible?

I don't deserve this. What have I done to you besides messing with your "amazing, dependable" boyfriend's head?

What happened to you not loving him anymore? What happened to me?

Have you been writing to Dean this summer? Or was it just me? Have you been lying to him, too?

That must be it, because I don't see any other reason for you to be doing this to me. Did he tell you to stop talking to me? He's a bit possessive if you haven't figured it out yet.

And he's never going to love you like I do.

Yeah, I said it. I love you, Rory. I have since I came to dinner at your house the first night I was here.

Now I'm lost pining for some loser's girl while I have about a million other options.

I just met this girl, walking around town. Her name is Shane. I think I'll ask her out.

Jess

**AND SO BEGINS SEASON THREE.**

**See, my aim here was to get it as close to the start of season 3 as possible. So, as we all know, Rory and Jess DO get together! Yay!**


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